CA2213614C - Process for the distillation of alcohols - Google Patents
Process for the distillation of alcohols Download PDFInfo
- Publication number
- CA2213614C CA2213614C CA002213614A CA2213614A CA2213614C CA 2213614 C CA2213614 C CA 2213614C CA 002213614 A CA002213614 A CA 002213614A CA 2213614 A CA2213614 A CA 2213614A CA 2213614 C CA2213614 C CA 2213614C
- Authority
- CA
- Canada
- Prior art keywords
- alcohols
- distillation
- ethylhexanol
- ppm
- alkali metal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention pertains to a method of distillatory purification of C3-C10 alcohols wherein the alcohols are distilled at 150 to 200~ C in the presence of 10 to 1000 ppm hydroxide alkali.
Description
i,, CA 02213614 1997-08-22 WO 96/26173 ~- _ _ _PCT/EP96/00633 .1~~~ ~T". i. ~ 'l i ~..3 ~ ~ a.-...e ~, '~T T~ar~s~~~zt~=I
Description Process for the distillation of alcohols Aliphatic C3-Clo-alcohols, such as n-butanol and, in particular, 2-ethylhexanol, have a high economic import-s ante. These alcohols are preferably prepared by hydrofor-mylation of olefins with subsequent hydrogenation of the aldehydes formed as intermediates (example: propylene n/i-butyraldehyde ~ n/i-butanols) or by aldolization of straight-chain aliphatic aldehydes to give the correspon-ding unsaturated aldehydes and subsequent hydrogenation (example: n-butyraldehyde -> 2-ethylhexenal ~ 2-ethyl-hexanol). Summary descriptions are found in, e.g., Ullmann's Encyclopedia of Industrial Chemistry: "Alco-hols, Aliphatic" (Vol. A 1), "2-Ethylhexanol" (Vol. A 10) and "Butanols" (Vol. A 4).
Apart from as a solvent, n-butanol is principally used in the paints and coatings sector and for the preparation of carboxylic esters, in particular n-butyl acrylate and di-n-butyl phthalate (DBP).
Description Process for the distillation of alcohols Aliphatic C3-Clo-alcohols, such as n-butanol and, in particular, 2-ethylhexanol, have a high economic import-s ante. These alcohols are preferably prepared by hydrofor-mylation of olefins with subsequent hydrogenation of the aldehydes formed as intermediates (example: propylene n/i-butyraldehyde ~ n/i-butanols) or by aldolization of straight-chain aliphatic aldehydes to give the correspon-ding unsaturated aldehydes and subsequent hydrogenation (example: n-butyraldehyde -> 2-ethylhexenal ~ 2-ethyl-hexanol). Summary descriptions are found in, e.g., Ullmann's Encyclopedia of Industrial Chemistry: "Alco-hols, Aliphatic" (Vol. A 1), "2-Ethylhexanol" (Vol. A 10) and "Butanols" (Vol. A 4).
Apart from as a solvent, n-butanol is principally used in the paints and coatings sector and for the preparation of carboxylic esters, in particular n-butyl acrylate and di-n-butyl phthalate (DBP).
2-Ethylhexanol a.s principally required as the alcohol component for the preparation of di-2-ethylhexyl phthalate (DEHP) and 2-ethylhexyl acrylate.
For these fields of application - in particular the preparation of acrylic ester -.the use of high-purity alcohols is absolutely necessary. In the industrial preparation of the alcohols, the purification a.s exclusively performed by multistage fractional distilla-tion. The alcohols in this case are exposed to a thermal stress over a period of several hours, bottom tempera-tures of 150 to 200°C being generally employed. As a consequence thereof, in the distillation of aliphatic C3-Clo-alcohols such as butanol and 2-ethylhexanol, formatiori of the corresponding aldehydes occurs which can be Separated off only with high expenditure under'conven-tional conditions employed in the technique.
The object was therefore to find a simple process for the distillation of C3-Clo-alcohols which does not have these disadvantages.
Surprisingly, it has been found that addition of small amounts of alkali metal hydroxide suppresses the formation of the corresponding aldehydes during the workup by distillation and aldehydes already present are even eliminated.
The present invention therefore relates to a process for the purification of C3-Clo-alcohols by distillation, which comprises distilling the alcohols at 150 to 200°C in the presence of 10 to 1000 ppm of alkali metal hydroxide.
More particularly, the present invention relates to a process for the purification of C3-C1o-alcohols by distillation, the C3-Clo-alcohols having been contaminated by aldehydes, which comprises distilling the alcohols at 150 to 200°C in the presence of 10 to 1000 ppm of alkali metal hydroxide, extractive distillation being ruled out.
The C3-Clo-alcohols can be straight-chained or branched. Particularly important C3-Clo-alcohols to which the process of the invention can be applied are n-butanol and 2-ethylhexanol.
The alkali metal hydroxides are used preferably KOH
or NaOH. The amount of alkali metal hydroxide is generally 10 to 1000 ppm, preferably 10 to 200 ppm, in each case based on the amount of the alcohol used. Preferably, the alkali metal hydroxides are added in the form of an aqueous solution.
2a If columns are used in the distillation, these generally have 20 to 80 trays.
As the following examples show, the addition of alkali metal hydroxide greatly decreases or even completely prevents the formation of aldehydes during the distillation of the alcohols, without other undesirable side reactions or significant reduction of the alcohol content occurring.
Frequently, an aldehyde content already present in the alcohol used is even eliminated.
For these fields of application - in particular the preparation of acrylic ester -.the use of high-purity alcohols is absolutely necessary. In the industrial preparation of the alcohols, the purification a.s exclusively performed by multistage fractional distilla-tion. The alcohols in this case are exposed to a thermal stress over a period of several hours, bottom tempera-tures of 150 to 200°C being generally employed. As a consequence thereof, in the distillation of aliphatic C3-Clo-alcohols such as butanol and 2-ethylhexanol, formatiori of the corresponding aldehydes occurs which can be Separated off only with high expenditure under'conven-tional conditions employed in the technique.
The object was therefore to find a simple process for the distillation of C3-Clo-alcohols which does not have these disadvantages.
Surprisingly, it has been found that addition of small amounts of alkali metal hydroxide suppresses the formation of the corresponding aldehydes during the workup by distillation and aldehydes already present are even eliminated.
The present invention therefore relates to a process for the purification of C3-Clo-alcohols by distillation, which comprises distilling the alcohols at 150 to 200°C in the presence of 10 to 1000 ppm of alkali metal hydroxide.
More particularly, the present invention relates to a process for the purification of C3-C1o-alcohols by distillation, the C3-Clo-alcohols having been contaminated by aldehydes, which comprises distilling the alcohols at 150 to 200°C in the presence of 10 to 1000 ppm of alkali metal hydroxide, extractive distillation being ruled out.
The C3-Clo-alcohols can be straight-chained or branched. Particularly important C3-Clo-alcohols to which the process of the invention can be applied are n-butanol and 2-ethylhexanol.
The alkali metal hydroxides are used preferably KOH
or NaOH. The amount of alkali metal hydroxide is generally 10 to 1000 ppm, preferably 10 to 200 ppm, in each case based on the amount of the alcohol used. Preferably, the alkali metal hydroxides are added in the form of an aqueous solution.
2a If columns are used in the distillation, these generally have 20 to 80 trays.
As the following examples show, the addition of alkali metal hydroxide greatly decreases or even completely prevents the formation of aldehydes during the distillation of the alcohols, without other undesirable side reactions or significant reduction of the alcohol content occurring.
Frequently, an aldehyde content already present in the alcohol used is even eliminated.
In the examples, the term "low-boilers" refers to compo-nents which are free of 2-ethylhexanal and boil consider-ably lower (at least 20 to 40°C lower) than 2-ethyl-hexanol and may therefore readily be separated from this by distillation.' Similarly, the term "high-boilers"
refers to components which are free of 2-ethylhexanal and boil considerably higher (at least 20 to 40°C higher) than 2-ethylhexanol and may therefore likewise readily be separated from this by distillation.
Comparison Example 1 2-Ethylhexanol having a content of 60 ppm (0.006 by weight) of 2-ethylhexanal was heated at 180°C for 1 hour without addition of alkali metal hydroxide. After 10, 30 and 60 minutes, a sample was taken in each case .and analyzed. The results are given in Table 1. After 60 minutes, the 2-ethylhexanal content was 140 ppm (0.014%
by weight).
Example 1 The procedure was followed as in Comparison Example 1 with the sole exception that 50 ppm of KOIi were added to the 2-ethylhexanol before heating was begun. The results are again given in Table 1. After 30 minutes, the 2-ethylhexanal content was already below the analytical detection la.mit of 0.001 by weight.
refers to components which are free of 2-ethylhexanal and boil considerably higher (at least 20 to 40°C higher) than 2-ethylhexanol and may therefore likewise readily be separated from this by distillation.
Comparison Example 1 2-Ethylhexanol having a content of 60 ppm (0.006 by weight) of 2-ethylhexanal was heated at 180°C for 1 hour without addition of alkali metal hydroxide. After 10, 30 and 60 minutes, a sample was taken in each case .and analyzed. The results are given in Table 1. After 60 minutes, the 2-ethylhexanal content was 140 ppm (0.014%
by weight).
Example 1 The procedure was followed as in Comparison Example 1 with the sole exception that 50 ppm of KOIi were added to the 2-ethylhexanol before heating was begun. The results are again given in Table 1. After 30 minutes, the 2-ethylhexanal content was already below the analytical detection la.mit of 0.001 by weight.
Table 1 Start- Comparison Example Example 1 (50 ppm FtOH) ing (without alkali metal mat- hydroxide) erial Time after start prior Time after start to start 10 min 30 min 60 10 mia 30 min 60 min min Low- 0.216 0.212 0.211 0.212 0.208 0.209 0.207 boilers (~ by wt.) 2-Eth- 0.006 0.011 0.013 0.014 0.002 <0.001 <0.001 ylhexa-nal ( ~ by wt . ) 2-Eth- 99.646 99.644 99.643 99.64099.616 99.616 9.9.616 ylhex-anol (~ by wt.) High- 0.132 0.133 0.133 0.134 0.174 0.175 0.177 boilers ( ~ by wt . ) Comparison Example 2 663 g of 2-ethylhexanol of the composition below (in % by weight) are used in a 2 1 distillation flask a.n a packed laboratory column having a 1 m high packing of 3 mm VA
steel spirals:
Low-boilers 0.099 2-Ethylhexanal 0.001 2-Ethylhexanol 99 '170 High-boilers 0.130 At a column pressure of 100 mbar and a reflex ratio of 3:1, four distillation fractions each of 130 g and a 5th fraction of 65 g were taken off at the column top at a temperature of 118°C. The individual fractions were studied by gas chromatography:
Table 2 Fraction 1 2 3 4 5 Low- 0.010 0.006 0.003 0.011 0.008 boilers ( o by wt.) 2-Ethyl- 0.013 0.009 0.008 0.010 0.011 hexanal ( o by wt . ) 2-Ethyl- 99.863 99.980 99.986 99.975 99.977 hexanol ( % by wt . ) High- 0.114 0.005 0.003 0.004 0.004 boilers ( ~S by wt . ) The 2-ethylhexanal content in the distillation residue (78 .g) was below the analytical detection limit.
Example 2 The procedure was followed as in Comparison Example 2, with the sole exception that 66 mg of a 50~ strength aqueous KOH solution were added to the 2-ethylhexanol before the start of distillation. The individual frac-tions were again studied by gas chromatography:
steel spirals:
Low-boilers 0.099 2-Ethylhexanal 0.001 2-Ethylhexanol 99 '170 High-boilers 0.130 At a column pressure of 100 mbar and a reflex ratio of 3:1, four distillation fractions each of 130 g and a 5th fraction of 65 g were taken off at the column top at a temperature of 118°C. The individual fractions were studied by gas chromatography:
Table 2 Fraction 1 2 3 4 5 Low- 0.010 0.006 0.003 0.011 0.008 boilers ( o by wt.) 2-Ethyl- 0.013 0.009 0.008 0.010 0.011 hexanal ( o by wt . ) 2-Ethyl- 99.863 99.980 99.986 99.975 99.977 hexanol ( % by wt . ) High- 0.114 0.005 0.003 0.004 0.004 boilers ( ~S by wt . ) The 2-ethylhexanal content in the distillation residue (78 .g) was below the analytical detection limit.
Example 2 The procedure was followed as in Comparison Example 2, with the sole exception that 66 mg of a 50~ strength aqueous KOH solution were added to the 2-ethylhexanol before the start of distillation. The individual frac-tions were again studied by gas chromatography:
Table 3 Fraction 1 2 3 4 5 Low- 0.010 0.006 0.003 0.011 0.008 boilers ( % by wt.) 2-Ethyl- 0.003 0.002 0.001 0.001 0.001 hexanal ( % by wt . ) 2-Ethyl- 99.863 99.987 99.993 99.984 99.987 hexanol ( % by wt.) High- 0.124 0.005' 0.003 0.004 0.004 boilers ( % by wt . ) The 2-ethylhexanal content in the distillation residue (78 g) was below the analytical detection limit.
Claims (3)
1. A process for the purification of C3-C10-alcohols by distillation, the C3-C10-alcohols having been contaminated by aldehydes, which comprises distilling the alcohols at 150 to 200°C in the presence of 10 to 1000 ppm of alkali metal hydroxide, extractive distillation being ruled out.
2. The process as claimed in claim 1, wherein, the C3-C10-alcohols are selected from the group consisting of n-butanol and 2-ethylhexanol.
3. The process as claimed in claim 1 or 2, wherein the alcohols are distilled in the presence of 10 to 200 ppm of alkali metal hydroxide.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19506280A DE19506280A1 (en) | 1995-02-23 | 1995-02-23 | Process for the distillation of alcohols |
| DE19506280.9 | 1995-02-23 | ||
| PCT/EP1996/000633 WO1996026173A1 (en) | 1995-02-23 | 1996-02-14 | Method for distilling alcohols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2213614A1 CA2213614A1 (en) | 1996-08-29 |
| CA2213614C true CA2213614C (en) | 2001-07-03 |
Family
ID=7754820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002213614A Expired - Fee Related CA2213614C (en) | 1995-02-23 | 1996-02-14 | Process for the distillation of alcohols |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6117277A (en) |
| EP (1) | EP0869936B1 (en) |
| JP (1) | JP3806146B2 (en) |
| KR (1) | KR100410705B1 (en) |
| CN (1) | CN1074403C (en) |
| AT (1) | ATE195503T1 (en) |
| AU (1) | AU702668B2 (en) |
| BR (1) | BR9607105A (en) |
| CA (1) | CA2213614C (en) |
| DE (2) | DE19506280A1 (en) |
| DK (1) | DK0869936T3 (en) |
| ES (1) | ES2151147T3 (en) |
| FI (1) | FI973433A0 (en) |
| IN (1) | IN186279B (en) |
| MX (1) | MX9706195A (en) |
| MY (1) | MY115717A (en) |
| PL (1) | PL182127B1 (en) |
| PT (1) | PT869936E (en) |
| RO (1) | RO117845B1 (en) |
| WO (1) | WO1996026173A1 (en) |
| ZA (1) | ZA961408B (en) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19809493A1 (en) * | 1998-03-05 | 1999-09-09 | Basf Ag | Process for the distillation of mixtures containing butanediol |
| DE10024542A1 (en) | 2000-05-18 | 2001-11-22 | Basf Ag | Production of saturated 3-20C alcohols uses a hydrogenation catalyst bed in the presence of a salt-like base in the reactant feed containing an anion of an acid having a pKa of greater than 2 |
| JP2002047225A (en) * | 2000-07-27 | 2002-02-12 | Mitsubishi Gas Chem Co Inc | Method for distilling polycyclic diol compounds |
| GR1003703B (en) * | 2000-12-27 | 2001-10-23 | Celanese Chemicals Europe Gmbh | Method for distilling alcohols |
| DE10161597B4 (en) * | 2001-12-14 | 2005-10-20 | Celanese Chem Europe Gmbh | Process for the purification of alicyclic alcohols |
| DE10252173B3 (en) * | 2002-11-09 | 2004-06-03 | Celanese Chemicals Europe Gmbh | Process for the recovery of aliphatic C3-C10 alcohols from high boilers |
| WO2009017936A1 (en) * | 2007-07-30 | 2009-02-05 | Dow Global Technologies Inc. | Process of refining c6-16 aliphatic diols |
| US8764946B2 (en) | 2009-03-19 | 2014-07-01 | Lg Chem, Ltd. | Dividing wall distillation columns for production of high-purity 2-ethylhexanol and fractionation method using same |
| EP2341041B1 (en) | 2009-12-24 | 2015-05-27 | Oxea Bishop LLC | Trimethylolpropane color improvement |
| IN2014CN03491A (en) | 2011-10-14 | 2015-07-03 | Toray Industries | |
| WO2014018837A1 (en) * | 2012-07-26 | 2014-01-30 | Cheng Cecilia | Butanol purification |
| US10112122B2 (en) | 2013-01-16 | 2018-10-30 | Lg Chem, Ltd. | Device for preparing alkanol |
| US9926248B2 (en) * | 2013-07-02 | 2018-03-27 | Basf Se | Process for the preparation of 3-heptanol from a mixture containing 2-ehthylhexanal and 3-heptyl formate |
| JP6088922B2 (en) * | 2013-07-03 | 2017-03-01 | 花王株式会社 | Method for producing Gerve alcohol |
| US9512054B2 (en) | 2015-02-10 | 2016-12-06 | Eastman Chemical Company | Method for making a high purity alcohol |
| CN105001046A (en) * | 2015-07-09 | 2015-10-28 | 武汉工程大学 | Nonyl alcohol synthesis process |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE142708C (en) * | ||||
| GB253128A (en) * | ||||
| US1600437A (en) * | 1924-08-05 | 1926-09-21 | Texas Co | Purification of crude alcohols |
| US2533753A (en) * | 1947-02-27 | 1950-12-12 | Kearney & Trecker Corp | Machine tool control mechanism |
| US2533754A (en) * | 1947-11-04 | 1950-12-12 | Shell Dev | Purification process |
| US2626284A (en) * | 1949-09-17 | 1953-01-20 | Standard Oil Dev Co | Aqueous caustic treat of iso-octyl alcohol |
| US2753297A (en) * | 1952-02-28 | 1956-07-03 | Exxon Research Engineering Co | Process for removal of sulfur impurities from alcohols |
| US2889375A (en) * | 1956-05-21 | 1959-06-02 | Gulf Research Development Co | Method of distilling alcohols |
| US3359335A (en) * | 1964-05-13 | 1967-12-19 | Exxon Research Engineering Co | Caustic scrubbing of aldox alcohols |
| US3576891A (en) * | 1967-11-06 | 1971-04-27 | Atlantic Richfield Co | Removal of esters and acids from tertiary-butyl alcohol solutions |
| AT283295B (en) * | 1967-12-20 | 1970-07-27 | Basf Ag | Process for the production of butanols |
| US3960672A (en) * | 1971-02-09 | 1976-06-01 | Veba-Chemie Ag | Continuous distillation process for purifying alkanols |
| US3990952A (en) * | 1974-10-10 | 1976-11-09 | Raphael Katzen Associates International, Inc. | Alcohol distillation process |
| DD228542A1 (en) * | 1984-11-09 | 1985-10-16 | Leuna Werke Veb | PROCESS FOR RECOVERING PROPANOL-1 |
| US5312950A (en) * | 1993-08-31 | 1994-05-17 | Eastman Kodak Company | Method for purification of alcohols |
| FR2713110B1 (en) * | 1993-12-03 | 1996-02-16 | Pierre Chevreux | Cleaning product for printing cylinders. |
-
1995
- 1995-02-23 DE DE19506280A patent/DE19506280A1/en not_active Withdrawn
-
1996
- 1996-02-12 IN IN256CA1996 patent/IN186279B/en unknown
- 1996-02-14 BR BR9607105A patent/BR9607105A/en active Search and Examination
- 1996-02-14 ES ES96904777T patent/ES2151147T3/en not_active Expired - Lifetime
- 1996-02-14 KR KR1019970705773A patent/KR100410705B1/en not_active IP Right Cessation
- 1996-02-14 DK DK96904777T patent/DK0869936T3/en active
- 1996-02-14 MX MX9706195A patent/MX9706195A/en not_active IP Right Cessation
- 1996-02-14 AT AT96904777T patent/ATE195503T1/en not_active IP Right Cessation
- 1996-02-14 AU AU48760/96A patent/AU702668B2/en not_active Ceased
- 1996-02-14 JP JP52536996A patent/JP3806146B2/en not_active Expired - Fee Related
- 1996-02-14 US US08/894,601 patent/US6117277A/en not_active Expired - Lifetime
- 1996-02-14 DE DE59605765T patent/DE59605765D1/en not_active Expired - Lifetime
- 1996-02-14 CN CN96192097A patent/CN1074403C/en not_active Expired - Fee Related
- 1996-02-14 RO RO97-01500A patent/RO117845B1/en unknown
- 1996-02-14 EP EP96904777A patent/EP0869936B1/en not_active Expired - Lifetime
- 1996-02-14 CA CA002213614A patent/CA2213614C/en not_active Expired - Fee Related
- 1996-02-14 WO PCT/EP1996/000633 patent/WO1996026173A1/en active IP Right Grant
- 1996-02-14 PT PT96904777T patent/PT869936E/en unknown
- 1996-02-14 PL PL96321896A patent/PL182127B1/en unknown
- 1996-02-17 MY MYPI96000636A patent/MY115717A/en unknown
- 1996-02-22 ZA ZA9601408A patent/ZA961408B/en unknown
-
1997
- 1997-08-21 FI FI973433A patent/FI973433A0/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US6117277A (en) | 2000-09-12 |
| PT869936E (en) | 2000-12-29 |
| DK0869936T3 (en) | 2000-11-20 |
| AU4876096A (en) | 1996-09-11 |
| CA2213614A1 (en) | 1996-08-29 |
| ATE195503T1 (en) | 2000-09-15 |
| EP0869936B1 (en) | 2000-08-16 |
| DE19506280A1 (en) | 1996-08-29 |
| PL182127B1 (en) | 2001-11-30 |
| FI973433A (en) | 1997-08-21 |
| BR9607105A (en) | 1997-11-04 |
| ZA961408B (en) | 1997-11-24 |
| RO117845B1 (en) | 2002-08-30 |
| DE59605765D1 (en) | 2000-09-21 |
| CN1074403C (en) | 2001-11-07 |
| PL321896A1 (en) | 1997-12-22 |
| CN1175939A (en) | 1998-03-11 |
| IN186279B (en) | 2001-07-28 |
| KR19980702375A (en) | 1998-07-15 |
| JPH11500437A (en) | 1999-01-12 |
| MY115717A (en) | 2003-08-30 |
| ES2151147T3 (en) | 2000-12-16 |
| MX9706195A (en) | 1997-11-29 |
| FI973433A0 (en) | 1997-08-21 |
| EP0869936A1 (en) | 1998-10-14 |
| KR100410705B1 (en) | 2004-03-30 |
| WO1996026173A1 (en) | 1996-08-29 |
| AU702668B2 (en) | 1999-02-25 |
| JP3806146B2 (en) | 2006-08-09 |
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